Under Sail from Sicily to the Riviera

Palermo is the Mediterranean's most intoxicating crossroads of civilisations — Arab arches meet Byzantine gold mosaics beneath Norman royal chapels in the extraordinary Palatine Chapel, a monument to 12th-century multicultural brilliance that is Sicily's single greatest work of art. The Ballarò and Capo street markets, among southern Italy's most atmospheric, tumble through the ancient city in a sensory barrage of swordfish, blood oranges, jasmine, and street food improvised across centuries. Do not leave without tasting arancini and sfincione, Sicily's gloriously thick street pizza. Spring (April–May) and autumn (September–October) offer the ideal climate — warm enough for the sea, cool enough for extended walking.

Lipari, the largest of Sicily's volcanic Aeolian Islands, has been a Mediterranean trading hub for over 6,000 years, featuring a dramatic Castello, world-class archaeological museum, and gateway access to Stromboli's erupting crater. Must-dos include exploring the fortified old town, tasting caper-laced Aeolian cuisine and Malvasia wine, and island-hopping to Vulcano and Stromboli. May through October offers ideal conditions.

Stromboli is an active volcanic island in the Aeolian archipelago that has erupted continuously for over two thousand years, earning its nickname as the Lighthouse of the Mediterranean. Must-dos include witnessing nighttime eruptions from the sea, hiking to the Sciara del Fuoco viewpoint, and tasting salt-cured capers and Malvasia wine on a terrace beneath the glowing summit. May through October offers calm seas and clear skies for the best eruption viewing.

Amalfi is the former maritime republic that gave its name to Italy's most celebrated coastline, where the Arab-Norman cathedral, medieval paper mills, and whitewashed buildings cascading to the Tyrrhenian Sea create the definitive image of Italian coastal beauty. Visit April through June via Windstar or Azamara for the Cloister of Paradise and the coastline that has been the world's standard for scenic perfection.

Ponza is a volcanic island in the Tyrrhenian Sea where pastel houses climb tufa cliffs above a crescent harbour, Roman fish pools hide in sea caves, and the freshest seafood in Italy arrives daily at waterfront restaurants. Visit from May through October for swimming in crystalline waters, exploring dramatic coastline by boat, and experiencing an Italian island untouched by mass tourism.

Portoferraio is the historic capital of Elba, the Tuscan island famous as Napoleon's place of exile, featuring Medici fortifications, pastel waterfront facades, and over 150 beaches. Must-dos include Napoleon's Villa dei Mulini, the Monte Capanne cable car, and sampling Aleatico dessert wine. May through October offers ideal Mediterranean conditions, with June and September best for avoiding crowds.

Portovenere is a fortified Ligurian fishing village at the entrance to the Gulf of Poets, where Byron and Shelley found inspiration among colorful harbor houses, a dramatic cliff-top church, and UNESCO-listed coastal landscapes. Must-dos include the Church of San Pietro, boat trips to Palmaria island, and tasting fresh gulf mussels with Cinque Terre wine. May, June, and September offer ideal weather with fewer crowds.

Portofino is a jewel-box fishing village on Italy's Ligurian coast, renowned for its pastel harbour, Castello Brown fortress views, and exquisite pesto-dressed trofie pasta at waterside trattorias. Visitors should walk the coastal trail to the Cristo degli Abissi underwater statue at San Fruttuoso and savour focaccia di Recco with a glass of local Vermentino. The ideal season stretches from late April through October, with September offering the perfect balance of warm Mediterranean light and the intimate calm that returns after summer's peak.

The port of Nice is a vibrant gateway to the French Riviera, offering a rich tapestry of history, stunning architecture, and delectable local cuisine. Must-do experiences include savoring local specialties at the bustling Cours Saleya Market and exploring the charming streets of Vieux Nice. The best time to visit is during the spring and early fall when the weather is mild and the city is alive with cultural festivities.